Lauryn Hill

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Milli Vanilli may have proved that the Grammys are terrible at evaluating talent, but Lauryn Hill showed that even they are capable of getting it right once in a while. In 1998, Hill’s stunning debut album The Miseducation of Lauryn Hill owned the Grammys, winning in five of the 10 categories for which it was nominated, including Best New Artist and Album of the Year. In this case, it wasn’t the Grammys’ fault that this would be her only appearance -- after that dizzying success, Hill went off the deep end, releasing the bizarre MTV Unplugged No. 2.0 in 2002, which has been described in many publications as an on-stage nervous breakdown. Hill has only made rare public appearances since then, becoming one of the all-time most mysterious of past Grammy winners.